A diastereoselective zinc-mediated propargylation of non-enolizable norbornyl α-diketones and an efficient AgI-catalyzed cycloisomerization of the resulting α-keto homopropargyl alcohols with terminal alkynes leading to spirocyclic dihydrofurans have been reported. The dihydrofurans obtained were subjected to hydrogenation to afford spiro tetrahydrofuran derivatives in nearly quantitative yields (98–99 %). Eventually, the prepared α-spiro tetrahydrofuran norbornyl monoketones were utilized as precursors for acid-mediated Grob-type fragmentation reactions and converted into 1-oxaspiro[4.5]decan-6-one derivatives by treatment with p-toluenesulfonic acid. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim